Polysulfone condensation polymers and the preparation of same



United States Patent POLYSULFONE CONDENSATION POLYMERS AND THE PREPARATION OF SAME Algird Kreuchunas, Detroit, Mich.

No firawing. Application December 5, 1955 Serial No. 550,805

6 Claims cl. 260-793) .sulfonewvith a p-phcnylenedithiol under suitable conditions.

The resins of my invention conform to the formula where R, R and R" represent hydrogen or lower alkyl radical that is 1 to carbon atoms and n is from 50 to 900.

The resins of the invention can be prepared from previously known organic compounds by a novel synthetic route which I have discovered.

A method for the production of the resins of the invention can be diagrammatically represented as follows:

lR OH where R, R and R" and n have the same significance as listed above and where X and X are chlorine, bromine or iodine, Me is potassium or sodium and R' is lower alkyl that is l to 4 carbon atoms.

The essential step of my process consists of reacting a p,p'-dihalodiphenyl sulfone, such as p,p-dichlorodiphenyl sulfone, with an alkali metal p-phenylene dimercaptide, such as sodium p-phenylene dimercaptide, in a liquid alcoholic medium. The alcoholic medium can be methanol, ethanol or isopropanol. The halogen atoms of the p,p'-dihalodiphenyl sulfone can be chlorine, bromine or iodine.

The degree of polymerization (n equals 50 to 900) can be varied by introducing into the reaction mixture a material such as p-halophenyl methyl sulfone or p-halophenyl phenyl sulfone. These in effect, by having reactive groups at one end only, terminate the polymer chain at lower values of n, i. e., at lower molecular weights.

The resins of this invention may be further reacted with an oxidizing agent such as hydrogen peroxide in glacial acetic acid or by means of potassium permanganate as an added step after the initial polymerization has taken place.

2,822,351 Patented Feb. 4, 1958 These" oxidized resins; poly-p-phenylene Sl11fOI16S5 are particularly usefuli'n' ap1'alications, such as, coatings, films or molded articles requiring stability at highttemperaturest The resins of this invention are useful as intermediates in the preparation of poly-p-phcnyle'ne sulfones and as coating agents.

In order to better understand the invention reference should be had to the following illustrative examples. Parts are-givenby weight unless other-wise specified;

Example 1 To a solution of 54 parts of sodium-methoxide-irr 800 parts by volume of methanol there is added 7 1' arser p-phenylenedithiol (1,4-dithiohydroquinone). p,p' Dichlorodiphenyl sulfone (1435 parts) is then added in one portion. The reaction mixture is refluxed for a period of four hours, cooled and poured in'to 20'00 parts by volume of water. The desired product is collected by filtration, washedwith water and dried; The product has the-fo'rmula so ss where it is 30016900.

Example 2 mula G -Q where n is 50 to 500.

It is obvious that many variations may be made in the products of this invention without departing from the spirit and scope thereof as defined in the appended claims.

I claim:

1. A polymeric condensation product of equal mole amounts of a p,p'-dihalodiphenyl sulfone of the formula where X and X are members of the group consisting of chlorine, bromine and iodine and where R and R are members of the group consisting of hydrogen, methyl and ethyl, with an alkali metal p-phenylene dimercaptide of the formula MOS --SMe where Me is a member of the group consisting of potassium and sodium and R" is a member of the group consisting of hydrogen, methyl and ethyl.

2. A polymeric condensation product of equal mole amounts of a p,p'-dihalodiphenyl sulfone of the formula where X and X have the same significance as in claim 1, with an alkali metal p-phenylene dimercaptide of the formula MeS SMe where Me has the same significance as in claim 1.

3. A polymeric condensation product of equal mole amounts of p,p'-dichlorodiphenyl sultone with sodium pphenylene dimercaptide.

v4. In a process for preparing a polymeric condensation product, the step of refluxing equal mole amounts of a p,p'-dihalodiphenylsulfone of the formula MeSGSMe where-Me is a member of the group consisting of potassium and sodium and R" is a member of the group consisting of hydrogen, methyl and ethyl, in a liquid alcoholic medium.

5. In a process for preparing a polymeric condensation product, the step of refluxing equal mole amounts of a p,p-dihalodiphenyl sulfone of the formula where X and X' have the same significance as in claim 4, with an alkali metal p-phenylene dimercaptide of the formula MeSOSMe where Me has the same significance as in claim 4, in a liquid alcoholic medium.

6. In a process for preparing a polymeric condensation product, the step of refluxing equal mole amounts of p,p'- dichlorodiphenyl sulfone with sodium p-phenylene dimercaptide in n-butanol.

' References Cited in the file of this patent UNITED STATES PATENTS, 1

Drake Apr. 25, 1944 Schoene Apr. '25, 1950 OTHER REFERENCES Chemical Abstracts, vol. 47, 1953, page March: 9548h. 

1. A POLYMERIC CONDENSATION PRODUCT OF EQUAL MOLE AMOUNTS OF A P,P''-DIHALODIPHENYL SULFONE OF THE FORMULA 